Application of emodin-3-acetic-acid to preparation of drugs for resisting herpes simplex virus type I

A technology of herpes simplex virus and emodin acetate, which is applied in antiviral agents, pharmaceutical formulas, medical preparations containing active ingredients, etc., can solve the problems of unreported treatment of herpes simplex virus and hinder the application of emodin, and achieve improvement Solubility, good druggability effect

Active Publication Date: 2019-03-29
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Modern pharmacological studies have found that emodin has anti-tumor activity, anti-microbial growth (such as staphylococcus, hemolytic streptococcus, etc.), antispasmodic, cough-relieving, immunosuppressive, diuretic, and diarrhea; it also has anti-influenza virus effects. , Hepatitis B virus, Coxsackie virus, rubella virus, etc., but there is no report on the treatment of herpes simplex virus type I
Emodin is insoluble in water, only soluble in alkali and some organic solvents such as ethanol, dimethyl sulfoxide (DMSO), which hinders the application of emodin in clinical development

Method used

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  • Application of emodin-3-acetic-acid to preparation of drugs for resisting herpes simplex virus type I
  • Application of emodin-3-acetic-acid to preparation of drugs for resisting herpes simplex virus type I
  • Application of emodin-3-acetic-acid to preparation of drugs for resisting herpes simplex virus type I

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The preparation method of 3-emodin acetate described in the present invention is obtained by referring to [Example 1] of the specific implementation method in the specification of ZL201510974947.7. Its preparation reaction formula is as follows figure 1 shown.

[0019] Take 125mg of emodin and 138mg of potassium carbonate, add 5mL of acetone, mix well, then add 71mg of α-bromoacetate methyl ester dropwise, and react under reflux at 50°C. After the reaction, add hydrochloric acid to adjust the pH value to 1-2, filter to obtain a red solid, and dry it in a vacuum oven at 40°C. Add 34.7mg of sodium hydroxide and 15mL of ethanol to a round-bottomed flask with 74.3mg of the product, stir at 30°C for 4h, put the reaction solution until no liquid precipitates, add 10ml of water to dilute, adjust the pH value to 1-2 with hydrochloric acid, and use ethyl acetate to The aqueous phase was extracted with ester, and the organic phases were combined, dried over sodium sulfate and a...

Embodiment 2

[0021] Determination of Cytotoxicity of 3-Emodin Acetate by MTT Method

[0022] Add 100 μL of 3-emodin acetate solution diluted to different concentrations (0.1 μM, 1 μM, 10 μM, 100 μM, 1000 μM) with DMEM (containing 2% fetal bovine serum, V / V) to the growing monolayer of Hep-2 cells, Cultivate for 48h. Cells not treated with 3-emodin acetate (adding 100 μL of DMEM containing 2% fetal calf serum) served as the normal control group. Detect the absorbance values ​​of the normal control group and the drug group by the MTT method, and calculate the cell survival rate (cell survival rate=average absorbance value of the drug group / average absorbance value of the normal control group×100%) to evaluate the cytotoxic effect of 3-emodin acetate .

[0023] The results showed that the cytotoxic effect of 3-acetate emodin on Hep-2 cells was as follows: cell adhesion, rounding, breaking and shedding, increase of intracytoplasmic granules, enhancement of refraction and obvious decrease of ...

Embodiment 3

[0025] The anti-HSV-1 effect of 3-emodin acetate in vitro, and the effect of concentration and dose

[0026] HSV-1 standard strain KOS strain (100PFU / ml) infected Hep-2 cells for 2 hours (using fluorescence real-time quantitative PCR and plaque assay to determine the establishment of HSV-1 infected cell model), different concentrations (2.5μmol / L , 5 μmol / L, 10 μmol / L, 20 μmol / L) 3-acetate emodin solution was used to treat the cells for 48 hours, and the cells were collected after 48 hours. 20 μM acyclovir (ACV) was used as a positive control, and water was used as a blank control (Con). Detect the expression of HSV-1gD mRNA in cells by fluorescent real-time quantitative PCR and he plaque assay to detect the formation of plaques in cell plates, and determine the antiviral effect of 3-acetate emodin on HSV-1 from two perspectives of viral nucleic acid and virus titer effect. Specific steps are as follows:

[0027] (1) Fluorescent real-time quantitative PCR was used to detect ...

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Abstract

The invention provides an application of emodin-3-acetic-acid to preparation of drugs for resisting herpes simplex virus type I, and belongs to the technical field of antiviral drugs. According to theprovided emodin-3-acetic-acid, hydroxyl on C3 of emodin is replaced with acetate, so that the solubility is greatly improved, and the emodin-3-acetic-acid has good druggability. Experiment proves that the emodin-3-acetic-acid has low toxins to Hep-2 cells infected with HSV-1 toxin strains, the gene expression of HSV-1 gD in the Hep-2 cells can be notably reduced by the emodin-3-acetic-acid, and besides, the duplication and infection of the HSV-1 in the Hep-2 cells are restrained. The emodin-3-acetic-acid has concentration dosage effects. The prepared emodin-3-acetic-acid has notable characteristic of resisting HSV-1 viruses, and becomes a drug candidate for clinical treatment of symptoms infected with the HSV-1 viruses.

Description

technical field [0001] The invention belongs to the technical field of antiviral drugs, and in particular relates to the application of 3-acetate emodin in the preparation of anti-herpes simplex virus type I drugs. Background technique [0002] Herpes simplex virus type I (HSV-1) is the most common human pathogen, and humans are its only natural host. It can cause latent or genital herpes, conjunctivitis, herpes eczema, and even death High rate of herpetic encephalitis. AIDS co-infection with HSV-1 will complicate HIV treatment. Most oral and genital herpes infections are asymptomatic, and herpes symptoms include painful blisters or sores at the site of infection. Herpes infection is most contagious once symptoms appear, but it can still be transmitted to others without symptoms, making it highly contagious. [0003] Most current therapies against HSV-1 virus infection use nucleotide, nucleoside or pyrophosphate analogues, such as acyclovir, valacyclovir, penciclovir and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/192A61P31/22
CPCA61K31/192A61P31/22
Inventor 侯炜施继春郑伟杰钟超洁蒋翠萍韩世宇洪学传程双王辉刘媛媛罗凡
Owner WUHAN UNIV
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